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Headshot of Sophia Amoruso in metallic jacket | Profile: Sophia Amoruso doesn't need a clean slate | Meridian by Mercury
Headshot of Sophia Amoruso in metallic jacket | Profile: Sophia Amoruso doesn't need a clean slate | Meridian by Mercury

Profiles and Q&As

Sophia Amoruso doesn’t need a clean slate

The accidental founder has made her fair share of mistakes — but she's turned them into a winning hand.

Written by Elizabeth Barton

Photography by Allison Nguyen

There’s a lot about Sophia Amoruso on the internet. Search her name and an entire tapestry of images, articles, and common Google queries arranges itself before your eyes. But for many of us, our mental image of this woman remains stuck on a static glimpse of who she used to be, on what she came to represent: a disgraced and ill-informed role model for female professionals who failed to live up to the values she so famously espoused.

But in speaking with Amoruso — or parsing through her social accounts and the countless articles that have been written about her to date — it seems that no matter how the world chooses to see her, Amoruso has moved beyond the point of caring. Rather than work tirelessly to convince others of something she has no control over, she’s mastered the art of applying past learnings and failures to new frontiers. She's focused on her impact rather than her image. Today, as a VC and education-focused business owner, she seeks to support people who find themselves as she once was: “an accidental and unlikely entrepreneur” who, as she tells me today, “had no idea what she was doing.”

Building a business is a risk, and no matter how meteoric your rise, there’s always a chance you can fall just as fast. Amoruso knows this firsthand. She also knows that a fall can lead to something even better on the other side.

Tracing Amoruso’s path from when she started Nasty Gal through to the present, we see a naturally imperfect person with superhuman resilience. A belief in tomorrow. Someone who isn’t afraid to pick up and try again, even ad infinitum.


It’s a weekday afternoon when I chat with Sophia. It was also a weekday afternoon when I first picked up #GIRLBOSS, her best-selling memoir. That was nearly 8 years ago, and I was a sophomore in college. By that point, I was already late to the hype. Published a year earlier in 2014, #GIRLBOSS had been making waves since it first hit shelves. It spent 18 weeks on the NYT bestseller list, and the book’s front cover — with a bold sans serif title placed above a power-stance photo of Amoruso — soon became recognizable to female millennials everywhere.

#GIRLBOSS was an inspiring, rags-to-riches tale. It chronicled Amoruso’s career, from those mythic early days circa 2006 when she started selling vintage clothes on eBay in her early twenties, to her position as the CEO and founder of a $200M company by her late twenties.

As a reader, it was difficult to imagine how someone could go from a life of dumpster diving and petty theft to the cover of Forbes as fast as Amoruso did, but the Amoruso of 2006 would have been just as surprised. When she started Nasty Gal, she had zero expectations and very little industry know-how. Through whatever combination of grit, luck, and vision it is that happens to produce retail magic, Amoruso rose swiftly from inexperienced obscurity to trusted commercial stardom. To industry players, she looked at ease. To her social media following, she looked like a relatable, cut-the-crap role model. We liked believing that any one of us could follow in her footsteps.

The best thing you could ever hope for is that you create something that goes out into the world and is so out of your control that it becomes part of the zeitgeist, that people can begin using the term however they want to.

#GIRLBOSS ushered in a fresh, social media-fueled brand of commercialized feminism the world hadn’t seen before, as well as renewed enthusiasm for female empowerment in the workplace. Amoruso’s memoir inspired young women in a way that Sheryl Sanberg’s Lean In (2013) hadn’t — namely, it proved you could have no formal experience in business and still succeed; you could have baby bangs and still command a boardroom. Capitalizing on the momentum her book created, Amoruso soon launched her own “girlboss” media company, began holding girlboss networking conferences, and started selling girlboss-branded merchandise. For thousands of inspired women, #GIRLBOSS became so much more than a book. It became a concept. It became a way of being.

“The best thing you could ever hope for,” Amoruso says, “is that you create something that goes out into the world and is so out of your control that it becomes part of the zeitgeist, that people can begin using the term however they want to.”

And that’s exactly what happened: Released into the ether, the term “girlboss” bounced back and forth between every corner of the internet, taking on new meaning with every reverberation. Initially touted as a means for female empowerment in the workplace (you’re such a girlboss!), the “girlboss” moniker eventually warped into a pejorative. The mere suggestion of this girlboss ideal became problematic. Why weren’t men called “boybosses”? Why did women need to adopt dogmatic male behaviors in order to succeed in the workplace? Critics dissected the term and all its connotations, eventually sending it to the expanding graveyard of words that culturally correct people no longer use — full stop.

News from Amoruso’s corner didn’t help: Nasty Gal — negatively affected by constant workplace turnover, claims of “toxic” leadership, and discrimination allegations — filed for bankruptcy in 2016, just two years after the publication of Amoruso’s memoir. In parallel, her name — and the girlboss brand — took a substantial hit. With time, an entire generation of young female CEOs and founders (including Emily Weiss of Glossier, Tyler Haney of Outdoor Voices, Audrey Gelman of The Wing, and Steph Korey of Away) were also pejoratively labeled “girlbosses.” In the eyes of their critics, these power-hungry women had actually done very little to promote healthy female entrepreneurship. In fact, Amoruso’s influence could be boiled down to a “remunerative quasi-feminist liberation fantasy,” and the disgraced girlbosses who followed — from Yael Aflalo of Reformation to Jen Gotch of — were all criticized for their supposed promotion of a “cool girl” leader who was left no room to be “anything but white and wealthy.”

Sophia Amoruso sitting on the floor of her home working on an iPad | Profile: Sophia Amoruso doesn't need a clean slate | Meridian by Mercury

“I think in some ways, I paved the way for a generation of female founders to fail,” Amoruso says. “But I was also held accountable to unrealistic expectations — expectations that male founders aren’t held to. I think the magnitude of my story and some of the cancellations of other female founders far outweighed the crimes that we committed.”

The initial “girlboss” hype may have been overblown, but criticism of the overall concept and its appointed figureheads potentially more so. It was idealistic — and arguably sexist — to believe that the mere presence of a woman in the driver’s seat could guarantee corporate utopia.

“It’s been 10 years,” Amoruso says. “I’m not the person I was when I wrote that book. I was much more naive, I was in my 20s. We were all less educated about workplace and gender dynamics, and that conversation has become even more nuanced since the book was written.”

Amoruso no longer considers herself a “girlboss” — nor does she plan on reclaiming this label in the future.

“I’ve pretty much divorced myself from the term. Not from the book; not from the impact it made; not from the inspiration it threw out into the world; not from the long-tail effect it had on women who still write to me saying ‘Oh my god, your book inspired me. I quit my job and started a business because I saw this average girl show me, for the first time, that I could do that, too.’ No one can measure the book’s influence, but I know the impact that it made. It’s something I’m really proud of.”

In the end, she says, the term “girlboss” and everything it brought to the table isn’t even about her. It’s about all of us and the world we live in. It was never intended as a panacea; it was always an imperfect way forward.

“If the term can be a conversation starter, an opportunity for people to have important conversations around feminism, race, privilege, hustle culture, lazy girl culture, or whatever — it’s fine by me.”

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As she speaks, Amoruso reflects on her storied past with the zen of someone who has processed it fully. Her outlook is nuanced. She’s embraced the ambiguity of everything that happened, the factors that were always out of her control.

If there was ever a massive story to tell around her successes and failures at Nasty Gal or in the aftermath of its fallout, today she wishes it could have been a story of someone doing her best and not always doing it right, or not having the information they needed to make the best decisions for their business.

The advice she gives other founders is the same advice she’s implemented in her own life: “If you make a mistake, just take the loss, learn from it, and move on. Because there’s just nothing else to do. Don’t go away,” she says. “Just try again.”

“It can feel like the world is watching you post-failure,” she continues. “But chances are, people are thinking about themselves and their own failures instead.”

Amoruso’s fall from grace was about as public as it can get, and she’s been open about its debilitating ramifications — not only in terms of her public image, but also in terms of her mental health. However, as the years have passed, Amoruso has come to realize that this retrospective amalgam of career highs and lows gives her an incisive advantage — both at work and beyond.

“I’m comfortable making mistakes and moving quickly,” she says, laughing as she admits that her resilience has proved useful in unexpected ways, including when she plays poker with her friends.

“People freak out when they lose a big hand, and I’m just like: That’s entirely my fault. I played it. I played it to the best of my ability. I missed something or I overestimated my hand or underestimated my opponent.”

Those who play a game like poker with her, she says, are always surprised to see how well she handles these losses. But to Amoruso, it’s a strong neural pathway. “I don’t expect to win all the time,” she shrugs. No matter where — or what — she’s playing, failure is a reality of life she’s become comfortable with.

“It’s better to fail early and to make a bunch of mistakes earlier in your business than to have this amazing rocket ship from day one,” she says.


Today, Amoruso’s biggest priority is helping other entrepreneurs who find themselves as she once was: a business novice who legitimately chanced upon entrepreneurship with no mentors, no context, and no formal education. Even as a full-time founder who would eventually achieve worldwide recognition and respect, she spent years hesitating to call herself an entrepreneur at all. She wants today’s aspiring or “accidental” entrepreneur to feel differently than she did; she wants them to wear that hat with confidence.

Part of instilling that sense of confidence, she says, centers on providing resources that can fill common knowledge gaps and help early-stage founders get their ideas off the ground — whether or not they have a traditional business background. That’s the entire premise of Business Class, Amoruso’s own “membership-based, digital entrepreneurship community and course for founders, freelancers, solopreneurs, creators, and side hustlers.”

Image of Sophia Amoruso playfully standing on table and couch in her home, balancing | Profile: Sophia Amoruso doesn't need a clean slate | Meridian by Mercury

Business Class members are promised they’ll learn what it takes to build a $100M business, which includes access to a rich community of 3,000+ active founders, 22 in-depth business lessons taught by Amoruso herself, live calls with Amoruso and other experts, virtual coworking sessions, and 80+ hours of interviews with CEOs, investors, attorneys, and social media specialists. The goal is to bring insider business knowledge to those who otherwise wouldn’t have it, and it’s designed for people who learn best from hands-on workshopping and real-world application.

Business Class is the type of all-in-one, virtual resource Amoruso wishes she’d been able to lean on earlier in her career, but it’s not the only resource she didn’t have.

“Back then, there was no Shopify or Squarespace or Cloud or Slack,” she says, reflecting. “[Tools like these] really help entrepreneurs in ways that didn’t exist when I started.” And software developments, she says, have “really democratized entrepreneurship — they make it possible for a wide variety of people to build businesses.”

Technology’s capacity for democratizing entrepreneurship was one of the main motivations behind Amoruso’s decision to start a venture capital fund. The north star of her work today — helping founders of all backgrounds — doesn’t stop at giving them the knowledge they need to make big ideas happen through Business Class. It’s also about putting money and energy behind ideas that directly impact these founders and the work they do.

Amoruso’s fund — playfully named Trust Fund as a nod to the trust fund so many of these founders never had but can build for themselves and their progeny in the future, she says — is specifically focused on funding early-stage startups working to create products that serve the needs of entrepreneurs, from traditional founders to the less traditional, such as freelancers, gig workers, and artists.

“With Trust Fund, I’m investing in companies that are building businesses for entrepreneurs. For instance,” she continues, “, [which I just invested in], is a gig marketplace for dental professionals to work on a shift basis at dental offices.” Even though this idea may not seem directly applicable to the traditional founder, it is working to create entrepreneurs, she says.

There are a lot of former operators who start funds, so for Amoruso to apply her experience with bootstrapping a business and raising money to her work as an investor isn’t necessarily groundbreaking. But today’s founders are familiar with Amoruso’s story to a degree that they aren’t familiar with the stories of other investors — and they can relate, on a much more intimate level, to where she’s been.

As for builders creating software for the express purpose of enabling entrepreneurs, it just so happens that the Sophia Amoruso of 15 years ago would have also been the target audience for their innovations.

“It’s not as simple as ‘I’m a former operator’ or ‘a former founder,’” she reiterates. “I’m a former accidental founder who not only didn’t have the products [these startups are building today], but who didn’t even know what I was supposed to do.

“My experience building Nasty Gal was a lot closer to the person who is starting a business in the creator economy than to the person who is raising $20M in venture capital,” she explains. “The ability of these products to demystify entrepreneurship for founders is so powerful. And I understand the end user and their blind spots better than I understand almost anything else.”

Would Amoruso’s trajectory have been different if she’d had access to more products like the ones she seeks to fund today as an investor? It’s impossible to say — but it doesn’t matter. Without having experienced the unique challenges of building without these tools, she wouldn’t have the firsthand understanding of founder pain points that many of today’s startups are looking to address.

“I have a million social followers across platforms who want to start businesses, who want to see what the latest software is, who are trying to choose between one ecommerce platform and another or understand programmatic SEO,” she says. “The fact that I’m able to [promote] the companies I invest in to a really relevant audience while also helping that audience — it feels great.”

Amoruso admits that even at this point in her career, it can still feel strange to consciously remember that she works in finance. But regularly advising early-stage companies as an investor and providing them with resources to help grow their businesses allows her to do her best work.

“I think I do my best at the early stage — that’s when companies are putting a brand together, that’s when founders are finding product-market fit. They’re talking to their customers and are really in the weeds, more than at any other point of the business journey. As an angel investor, most of my investments were at the seed stage and that was where I did really well,” she says. “This is my favorite stage of business … It’s just more fun.”


Amoruso does seem to be having fun. In fact, it seems like she’s thriving. And for those of us watching, her belief in the power of technology to remedy the challenges inherent to modern entrepreneurship is promising — and convincing.

But could technological developments ever fully resolve all of this path’s challenges? Even if every “technical” founder pain point could theoretically be solved, it seems unlikely that any human invention could put an end to what’s been a persistent theme throughout Amoruso’s career: that infamous state of feeling like you don’t belong; that nagging voice in your head that insists you don’t have a place in this world of building businesses; that pervasive and widespread sensation of imposter syndrome.

My experiences have given me a lot of perspective on what matters and what doesn’t. It’s taught me to be a lot more strategic with how I spend my time and when I put myself out there. It gives me an opportunity to share that experience with the founders I invest in. And if someone says something, then like, who cares?

Amoruso is famous for harnessing her own imposter syndrome and transforming it into her defining strength. And even a decade later, she still believes a healthy dose of imposter syndrome can prove to be a superpower. It’s not necessarily something we should be aiming to eliminate entirely — and why would we want to?

“I think the underdog mentality is a great one, as long as you don’t have a chip on your shoulder so heavy that it makes you lopsided,” she says. “Feeling underestimated is an opportunity to say, ‘Watch me pull this off.’ It’s an opportunity for you to carve out a unique space of your own.”

At this point in our conversation, I’m reminded of why I found Amoruso’s words so galvanizing when I first read #GIRLBOSS. Here, at a completely different stage in my life, I hear her speak and feel more or less exactly what I felt then. I don’t find her candor grating — it’s just realistic. As a friend, I sense she’d be the first person to tell you what she really thought; the first person to bring you back down to earth. And despite the development of her indomitable girlboss persona, she’d also be the first person to speak openly about her unrelenting self-doubt.

But this also begs the question: When you’ve arrived at the point of starting your own venture capital fund; when your fund’s LPs include names like Marc Andreessen, Jason Calacanis, Jeff Jordan, Andrew Chen, and Paris Hilton; and when you’re teaching other people the fundamentals of entrepreneurship with your own self-branded online course, can you still call yourself an outsider?

Some would say no, but to Amoruso, imposter syndrome can take form in unexpected ways. Just because you’ve had success in your field doesn’t mean you’ll never feel like an outsider again.

“There still aren’t as many women in the rooms I enter, especially in venture, and especially as a woman in finance with no formal education,” she says. “When you are the only ‘fill-in-the-blank’ in the room, you stand out whether or not it’s an advantage. But there will always be times that this is an advantage.”

On a routine basis, Amoruso is probably the only “I built a $200M company in my twenties in a male-dominated environment, was hailed as the face of a generation of female entrepreneurs, and then heavily criticized for not being perfect” person in many of the rooms she enters. And today — just like when she built Nasty Gal — she brings something invaluable to venture capital because of it.

“My experiences have given me a lot of perspective on what matters and what doesn’t,” she says. “It’s taught me to be a lot more strategic with how I spend my time and when I put myself out there. It gives me an opportunity to share that experience with the founders I invest in. And if someone says something, then like, who cares?”

It’s easy to say you wouldn’t care, even if you would. But when Amoruso says she wouldn’t care, you can tell she means it. In her mind, any kind of criticism, failure, or snarky social media comment is just part of the ride.

And at this point, it’s clear: Amoruso has always been ready to try a new roller coaster.

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